@Delirium: So the course of events is:
• In order to trigger
One Way or Another you promised to serve as eyes and ears for Uskglass, this is a promise, not a Debt, so there is nothing mechanical enforcing that, but it will affect your reputation (if you are effective or not, if you follow through or not, if you brush it off, and so on, tells people about what sort of person you are).
• As a result of the above Move, Uskglass agrees to
Overlook a Harm, so you Owe him a Debt.
The promise provides the trigger for the Playbook Move, the Move snowballs into
Overlook, and
Overlook results in a Debt. The promise is just that, nothing more.
Fair?